9,10-Bis(chloromethyl)anthracene → 9,10-Anthracenedimethanamine, N,N'-bis(2-(dimethylamino)ethyl)-

HRID 2210934

Reaction equation

HRID 2210934 reaction equation
Cl[CH2:2][C:3]1[C:4]2[C:9]([C:10]([CH2:17]Cl)=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH2:23]>O>[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH:23][CH2:2][C:3]1[C:4]2[C:9]([C:10]([CH2:17][NH:23][CH2:22][CH2:21][N:20]([CH3:24])[CH3:19])=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 252199,10-Bis(chloromethyl)anthraceneHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 602429,10-Anthracenedimethanamine, N,N'-bis(2-(dimethylamino)ethyl)-Yield 36.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g (0.0036 mol) of 9,10-dichloromethylanthracene (0.0036 mol) is refluxed for 20 minutes with 15 g of 2-dimethylaminoethylamine. The reaction mixture is added to water and the precipitate collected by filtration. The dried solid is then recrystallised from ethyl acetate to yield 0.5 g of the title compound as yellow crystals, m.p. 58°-60° C.; λmax (distilled water) (E/cm/M) 248 nm (51760), 372 nm (9030), 392 nm (8305).

Workup

  1. filtrationthe precipitate collected by filtration
  2. customThe dried solid is then recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-1627f4ee3e49405582af87ecf97f6654
Source dataset
uspto-grants-1995_10
Patent number
US05461078

Linked notes

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